Synthesis of beta-lactams bearing functionalized side chains from a readily available precursor.
The reaction of chlorosulfonyl isocyanate (CSI) with alkenes provides beta-lactams in quantity, and the products have frequently been used for ring-opening polymerization to generate nylon-3 materials. Prior uses of this approach have focused almost entirely on beta-lactams with purely hydrocarbon substitutents. We show how a variety of beta-lactams bearing protected polar substituents can be generated from CSI-derived building blocks.
Lee
Myung-ryul
MR
Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53706, USA.
Stahl
Shannon S
SS
Gellman
Samuel H
SH
D000588:Amines / Q000737:chemistry; D006878:Hydroxides / Q000737:chemistry; D017953:Isocyanates / Q000737:chemistry; D047090:beta-Lactams / Q000138:chemical synthesis* / Q000737:chemistry
D000588:Amines; D006878:Hydroxides; D017953:Isocyanates; D047090:beta-Lactams; C487390:chlorosulfonyl isocyanate; C031356:hydroxide ion